22217-80-7

Usage

Uses

Used in Pharmaceutical Industry:
5-(4-Methoxy-Phenyl)-3,4-Dihydro-2H-Pyrrole is used as a building block for the synthesis of pharmaceutical compounds due to its unique structural features and potential biological activity. Its complex structure allows for the development of new drugs with specific therapeutic properties.
Used in Agrochemical Industry:
In the agrochemical industry, 5-(4-Methoxy-Phenyl)-3,4-Dihydro-2H-Pyrrole is used as a precursor for the development of new agrochemicals. Its structural complexity and potential biological activity make it a valuable component in the creation of innovative and effective products for agricultural applications.
Used in Materials Science:
5-(4-Methoxy-Phenyl)-3,4-Dihydro-2H-Pyrrole is utilized in materials science for the development of new materials with unique properties. Its complex structure and potential for interaction with other molecules make it a promising candidate for the creation of advanced materials with specific characteristics for various applications.

InChI:InChI=1/C11H13NO/c1-13-10-6-4-9(5-7-10)11-3-2-8-12-11/h4-7H,2-3,8H2,1H3

Upstream product

• 189079-75-2 4-azido-1-(4-methoxyphenyl)butan-1-one 
• 7152-03-6 p-methoxyphenyl cyclopropyl ketone 
• 40877-19-8 4-chloro-1-(4-methoxyphenyl)butan-1-one 
• 14468-90-7 N-trimethylsilyl-pyrrolidin-2-one 
• 13139-86-1 4-methoxyphenyl magnesium bromide 
• 696-62-8 para-iodoanisole 
• 1491569-68-6 4-azido-1-(4-methoxyphenyl)butan-1-ol 
• 76-05-1 trifluoroacetic acid 
• 104-92-7 1-bromo-4-methoxy-benzene 
• 628-20-6 4-Chlorobutyronitrile 
• 164171-80-6 1-(4-methoxyphenyl)cyclobutan-1-ol 
• 583825-27-8 1-(4-azidobutyl)-4-methoxybezene 
• 727418-56-6 3-(4-methoxy-benzoyl)-1-vinyl-pyrrolidin-2-one 
• 94-30-4 ethyl 4-methoxybenzoate 

Downstream Products

• 108201-12-3 5-(4-Methoxyphenyl)-2,3-diphenyl-1-azabicyclo<3.3.0>oct-2-en-4-on 
• 111399-26-9 1-methyl-2-(4-methoxyphenyl)-1-pyrrolinium trifluoromethanesulfonate 
• 83314-44-7 5-(4-Methoxy-phenyl)-1-methyl-3,4-dihydro-2H-pyrrolium; iodide 
• 189079-91-2 4-Bromo-5-(4-methoxy-phenyl)-3,4-dihydro-2H-pyrrole 
• 189079-89-8 4,4-Dibromo-5-(4-methoxy-phenyl)-3,4-dihydro-2H-pyrrole 
• 189079-85-4 4,4-Dichloro-5-(4-methoxy-phenyl)-3,4-dihydro-2H-pyrrole 
• 1023299-40-2 2,2,2-trifluoro-1-[2-(4-methoxyphenyl)-4,5-dihydro-1H-pyrrol-3-yl]ethanone 
• 4995-12-4 2-(4-methoxyphenyl)-1H-pyrrole 
• 110014-90-9 7a-(4-Methoxy-phenyl)-2-methylene-hexahydro-pyrrolizine 
• 83314-57-2 4-(4'-Methoxyphenyl)-1-methyl-azacyclo-3-hepten 
• 83314-52-7 1-(4'-Methyoxyphenyl)-1-methyl-2-vinyl-pyrrolidin 
• 83314-48-1 2-(4-Methoxy-phenyl)-1-methyl-pyrrolidine-2-carbonitrile 
• 83334-46-7 4-(4'-Methoxyphenyl)-1,1-dimethyl-azacyclo-3-hepteniumiodid 
• 126328-77-6 C₁₅H₁₅⁽²⁾H₄NO 

Relevant academic research and scientific papers

Identification of the first structurally validated covalent ligands of the small GTPase RAB27A

Rab27A is a small GTPase, which mediates transport and docking of secretory vesicles at the plasma membrane via protein-protein interactions (PPIs) with effector proteins. Rab27A promotes the growth and invasion of multiple cancer types such as breast, lung and pancreatic, by enhancing secretion of chemokines, metalloproteases and exosomes. The significant role of Rab27A in multiple cancer types and the minor role in adults suggest that Rab27A may be a suitable target to disrupt cancer metastasis. Similar to many GTPases, the flat topology of the Rab27A-effector PPI interface and the high affinity for GTP make it a challenging target for inhibition by small molecules. Reported co-crystal structures show that several effectors of Rab27A interact with the Rab27A SF4 pocket ('WF-binding pocket') via a conserved tryptophan-phenylalanine (WF) dipeptide motif. To obtain structural insight into the ligandability of this pocket, a novel construct was designed fusing Rab27A to part of an effector protein (fRab27A), allowing crystallisation of Rab27A in high throughput. The paradigm of KRas covalent inhibitor development highlights the challenge presented by GTPase proteins as targets. However, taking advantage of two cysteine residues, C123 and C188, that flank the WF pocket and are unique to Rab27A and Rab27B among the >60 Rab family proteins, we used the quantitative Irreversible Tethering (qIT) assay to identify the first covalent ligands for native Rab27A. The binding modes of two hits were elucidated by co-crystallisation with fRab27A, exemplifying a platform for identifying suitable lead fragments for future development of competitive inhibitors of the Rab27A-effector interaction interface, corroborating the use of covalent libraries to tackle challenging targets. This journal is

Synthesis of 1-Pyrroline by Denitrogenative Ring Expansion of Cyclobutyl Azides under Thermal Conditions

We herein report an efficient and systematic synthesis of 1-pyrrolines from cyclobutyl azides under thermal and neutral conditions. The reaction proceeded without any additional reagents, and nitrogen was generated as the sole by-product. Furthermore, the generated 1-pyrrolines could be continuously transformed into pyrroles, N-Boc-amines, and oxaziridines in an one-pot manner. (Figure presented.).

Intramolecular Csp3-H/C-C bond amination of alkyl azides for the selective synthesis of cyclic imines and tertiary amines

The intramolecular Csp3-H and/or C-C bond amination is very important in modern organic synthesis due to its efficiency in the construction of diversified N-heterocycles. Herein, we report a novel intramolecular cyclization of alkyl azides for the synthesis of cyclic imines and tertiary amines through selective Csp3-H and/or C-C bond cleavage. Two C-N single bonds or a CN double bond are efficiently constructed in these transformations. The carbocation mechanism differs from the reported metal nitrene intermediates and therefore enables metal-free and new transformation.

Intramolecular Cyclization of Brominated Oxime Ether Promoted with Ytterbium(0) to the Synthesis of Cyclic Imines

The first utility of ytterbium(0) as a mediating-metal in the intramolecular cyclization of brominated oxime ether was reported in this paper. In contrast to the prior methods, the N–O bond was used as a receptor of nucleophilic reagent, rather than as a source of N-centered radicals. Cyclic imines were obtained in this one-pot reaction with a broad scope of substrates and feasible reaction conditions.

Design, synthesis and biological evaluation of N-hydroxy-aminobenzyloxyarylamide analogues as novel selective κ opioid receptor antagonists

Aminobenzyloxyarylamide derivatives 1a-i and 2a-t were designed and synthesized as novel selective κ opioid receptor (KOR) antagonists. The benzoyl amide moiety of LY2456302 was changed into N-hydroxybenzamide and benzisoxazole-3(2H)-one to investigate whether it could increase the binding affinity or selectivity for KOR. All target compounds were evaluated in radioligand binding assays for opioid receptor binding affinity. These efforts led to the identification of compound 1c (κ Ki = 179.9 nM), which exhibited high affinity for KOR. Moreover, the selectivity of KOR over MOR and DOR increased nearly 2-fold and 7-fold, respectively, compared with (±)LY2456302.

Enantioselective Imine Reduction Catalyzed by Phosphenium Ions

The first use of phosphenium cations in asymmetric catalysis is reported. A diazaphosphenium triflate, prepared in two or three steps on a multigram scale from commercially available materials, catalyzes the hydroboration or hydrosilylation of cyclic imin

Iminyl Radicals by Reductive Cleavage of N-O Bond in Oxime Ether Promoted by SmI2: A Straightforward Synthesis of Five-Membered Cyclic Imines

A new generation method of N-centered radicals from the reductive cleavage of the N-O bond in oxime ether promoted by SmI2 is reported for the first time. The in-situ-generated N-centered radicals underwent intramolecular cyclization to afford five-membered cyclic imines in two manners: N-centered radical addition and N-centered anion nucleophilic substitution. From a synthetic point of view, an efficient synthetic method of five-membered cyclic imines was developed. A mechanism of the transformation was proposed.

Preparation method of imine compound

The invention discloses a preparation method of an imine compound. The method comprises the following steps: under the anhydrous and anaerobic conditions, an oxime ether and a metal element are addedinto a reaction vessel in one pot, tetrahydrofuran is us

Method for synthesizing pyrroline compounds through iron-catalyzed amino alcohol and enol

The invention discloses a method for synthesizing pyrroline compounds through iron-catalyzed amino alcohol and enol. In the atmosphere of inert gas, the amino alcohol and the enol serve as raw materials, potassium tert-butoxide is used as alkali, a series

Design, synthesis and biological evaluation of aminobenzyloxyarylamide derivatives as selective κ opioid receptor antagonists

Opioid receptors play an important role in both behavioral and mood functions. Based on the structural modification of LY2456302, a series of aminobenzyloxyarylamide derivatives were designed and synthesized as κ opioid receptor antagonists. The κ opioid receptor binding ability of these compounds were evaluated with opioid receptors binding assays. Compounds 1a-d showed high affinity for κ opioid receptor. Especially for compound 1c, exhibited a significant Kivalue of 15.7?nM for κ opioid receptor binding and a higher selectivity over μ and δ opioid receptors compared to (±)LY2456302. In addition, compound 1c also showed potent κ antagonist activity with κ IC50?=?9.32?nM in [35S]GTP-γ-S functional assay. The potential use of the representative compounds as antidepressants was also investigated. The most potent compound 1c not only exhibited potent antidepressant activity in the mice forced swimming test, but also displayed the effect of anti-anxiety in the elevated plus-maze test.